Ask Jeeves borrowed a valet from P. G. Wodehouse's fiction and put him in charge of a search engine. Early search engines made people think like librarians and type keywords. Ask Jeeves let them type a question, as they would to a person. Editors behind the scenes matched common questions to good answers. When the company went public on July 1, 1999, the web was full of new users who found keyword search confusing.

Plain English Over Keywords

Garrett Gruener, a venture capitalist, and David Warthen, a software engineer, started the company in Berkeley in 1996. Their bet was that plain language would beat keywords. The system paired software that parsed questions with a large library of answers that people had written and checked. The cartoon butler on the home page gave the service a personality. By 1999 Jeeves was one of the best-known faces online.

Google Changes the Question

Ask Jeeves priced its offering at $14 a share on July 1, 1999, and the stock soared on its first day of trading. Google soon showed that good ranking mattered more than plain-language parsing. Ask Jeeves bought the Teoma search engine in 2001 to keep up. IAC acquired the company in 2005 for about $1.85 billion. The butler retired in 2006, and the service carried on as Ask.com.

Cover: Study of Valet with Coffee Pot, François Boucher. Art Institute of Chicago, public domain. Chosen for a valet with a coffee pot (the butler).